Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, a hidden gem nestled in the picturesque town of Highlands, North Carolina. This enchanting subdivision is renowned for its breathtaking mountain views, lush greenery, and a serene atmosphere that makes it a perfect retreat for nature lovers and those seeking a tranquil lifestyle.

Chestnut Hill offers a unique blend of rustic charm and modern convenience, with homes that reflect the beauty of the surrounding landscape. Each property is thoughtfully designed, featuring spacious layouts, high-quality finishes, and outdoor spaces that invite you to embrace the stunning natural surroundings. Whether you’re looking for a cozy cabin or a luxurious mountain home, Chestnut Hill has something to suit every taste and lifestyle.

The community is not just about beautiful homes; it’s also about the lifestyle. Residents enjoy access to an array of outdoor activities, from hiking and biking in the nearby Nantahala National Forest to exploring the scenic waterfalls and rivers that characterize the Highlands area. With a mild climate and four distinct seasons, outdoor enthusiasts will find endless opportunities for adventure year-round.

In addition to its natural beauty, Chestnut Hill is conveniently located near the charming downtown Highlands, where you can explore boutique shops, delightful eateries, and local art galleries. The sense of community here is palpable, making it easy to connect with neighbors and participate in local events.

If you’re ready to find your dream home in this idyllic setting, explore the homes for sale in Chestnut Hill today. Experience the perfect blend of mountain living and modern amenities—your sanctuary awaits!

Newest Chestnut Hill Homes for Sale

$749,000

3 Beds ⋅ 2 Baths ⋅ 1004129 MLS ⋅ ACTIVE Status

Move-In Ready! This thoroughly renovated 3 bedroom/2 bathroom cottage is one of the finest in Chestnut Hill and one of the most compelling values in Highlands. Enjoy low-maintenance, one-level mountain living in Chestnut Hill, a community in which exterior maintenance and landscaping are meticulously managed for you, permitting true “lock & leave” living just minutes from the fine shops and dining in Highlands town center. Enter through the private front-screened porch and step into the large, bright Great Room with stone fireplace that opens to the covered rear-deck perfect for entertaining. As you tour the home, you will note the extensive premium renovations throughout including the gourmet kitchen, two bathrooms, new flooring and upgraded finishes including custom trim and doors. The large primary suite features a large walk-in closet and truly luxurious bathroom featuring a top-of-the-line multi-function Toto toilet. There are two (2) guest bedrooms and full-size laundry with ample storage and closet space throughout. For convenience, there is an attached one-car garage and for guests there is ample additional parking. A dedicated back-up generator, proximity to Highlands’ healthcare campus and easy, paved access provide confidence year-round. Whether you are looking for a private retreat, an income property or both, 11 Wood Lily Way awaits. Highlands NC was selected by Travel & Leisure as “America’s Best Small Mountain Town” in 2023 and Outside magazine ranked Highlands as one of its top ten small adventure towns in the world for 2026. Recent updates and upgrades extend beyond the extensive interior remodel and include: • New Roof • Professionally encapsulated crawlspace with commercial dehumidifier • New heating and air-conditioning systems • Dual tankless hot water heaters • Back-Up Generator • Monitored underground propane tank. • Premium duo-fold (top-down, bottom-up) cellular window treatments

11 Woodlily Way, Highlands

Listing courtesy of Christie's International Real Estate Highlands-Cashiers.

Listing courtesy of Christie's International Real Estate Highlands-Cashiers

$675,000

3 Beds ⋅ 2 Baths ⋅ 1003978 MLS ⋅ ACTIVE Status

Enjoy refined, low-maintenance mountain living in Chestnut Hill—an ideal setting for those who value both ease and independence. Here, exterior home maintenance and landscaping are thoughtfully managed for you, freeing your time to enjoy the lifestyle rather than the upkeep. This single-level three-bedroom, two-bath residence offers the simplicity of condominium living with the privacy, space, and comfort of a detached home—complete with its own garage. Located just moments from Highlands-Cashiers Hospital and the heart of downtown Highlands, you will appreciate the convenience of nearby medical services, dining, and shopping, all while returning home to a peaceful mountain setting. Chestnut Hill is perfectly suited for those seeking a full-time residence or a lock-and-leave retreat without sacrificing comfort, accessibility, or charm. HOA dues cover road maintenance, snow removal, water, and sewer, giving you true low-maintenance living. Tucked away at the end of a quiet cul-de-sac, the home features an open floor plan with beautiful new wood flooring, exposed wood beams in the great room, fully remodeled bathrooms, and an updated kitchen with new cabinetry, countertops, and stainless-steel appliances. Located just minutes from downtown Highlands, the community also offers a welcoming activity center where neighbors regularly gather for food, fun, and fellowship.

55 Wood Lily Way, Highlands

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty.

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty

$675,000

2 Beds ⋅ 2 Baths ⋅ 1002858 MLS ⋅ ACTIVE Status

Life in the mountains often asks for a balance - beauty without burden, charm without complication- and this thoughtfully maintained cottage in the Chestnut Hill community delivers exactly that. Just minutes from the heart of Highlands and conveniently close to Highlands-Cashiers Hospital, the home offers a rare blend of accessibility and retreat. Whether it’s a morning coffee run into town, an evening dinner on Main Street, or the peace of mind that comes with nearby medical care, everything you need is effortlessly within reach. What sets this property apart is its simplicity of living. Though it is a single-family home, it lives with the ease and freedom of a lock-and-leave condominium - no constant upkeep, no lingering to-do lists, just the ability to come and go as you please, knowing your home remains as pristine as you left it. Inside, the atmosphere is light and welcoming. A vaulted ceiling elevates the living room, where natural light filters in and creates a sense of openness that feels both airy and grounded. The kitchen has been tastefully updated, offering generous storage and a comfortable breakfast nook that invites slow mornings and unhurried conversation. From here, the transition to the back patio is seamless - perfect for enjoying cool mountain air or a quiet evening outdoors. Two well-proportioned bedrooms and two full baths provide both comfort and privacy, whether hosting guests or enjoying a quiet weekend alone. An attached one-car garage adds another layer of convenience, offering protected parking along with valuable storage space. This is mountain living reimagined - not as a project, but as a pleasure. A place where the pace slows, the surroundings inspire, and homeownership feels refreshingly uncomplicated.

31 Chestnut Hl, Highlands

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty.

Listing courtesy of Berkshire Hathaway HomeServices Meadows Mountain Realty

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